If the goal is simply money, making it is not necessarily hard. There are many corporate positions that pay an obscene amount of money at the cost of being very dull. Somebody who enters a market with the goal of making money and nothing else is going to make a lot of money. Most of the routes available are much easier than the one that he picked, which requires a good idea and a lot of luck.
Alex was not slamming Sam's achievement. He just said that from a business perspective rather than a hacker's perspective, the hacker route to riches is very fraught and few people ever make it. You're an outlier, as is Sam, but statistically speaking, more people fail as hacker/entrepreneurs than fail as high-powered corporate lawyers or as cutthroat schmoozers. Even the moderate successes, like Sam (moderate being relative to, say, the people who created Facebook/Microsoft/Google), aren't particularly better-off than the people who merely submit to the system and work their asses off, so the risk doesn't pay a higher financial reward. The only reward is that of personal fulfillment.